


Who's Counting?

by galadreel



Category: Supernatural
Genre: Alternate Universe - Human, Alternate Universe - Romantic Comedy, Bisexual Dean, F/F, F/M, Friends to Lovers, M/M
Language: English
Status: In-Progress
Published: 2014-07-30
Updated: 2014-08-14
Packaged: 2018-02-11 00:39:19
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 10,894
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2046426
Author URL: https://archiveofourown.org/users/galadreel/pseuds/galadreel
Summary: <blockquote class="userstuff">
              <p>A What's Your Number? AU</p><p>Dean needs a date to his brother's wedding, so he enlists the help of his neighbor Castiel to track down his exes for a shot at a second chance.</p>
            </blockquote>





	1. Chapter 1

**Notes for the Chapter:**

> if you've seen What's Your Number? you know to expect a whole hell of a lot of Dean/Other, as well as some Cas/Other, although those won't be detailed. don't worry! there's plenty of Dean/Cas interaction (not so much in this chapter, however).
> 
> obviously, neither Supernatural nor What's Your Number? belong to me.

“So, you know Sam’s wedding is coming up,” Dean says hesitantly. His eyes flick over to Anna, curled up on the other side of the bed. Anna makes a sound that isn’t quite a word, not quite a grunt. She isn’t a morning person. Dean feels her shift and stretch her legs. She sits up to look down at him, pulling a strand of red hair out of her mouth.

“You’ve mentioned it,” she says. “Why’re you bringing it up at the crack of dawn?”

“It’s nine AM,” Dean counters. He has always been an early riser.

“Yeah, nine AM on _Saturday_ ,” she says, as if that explains everything. She throws off the sheet and saunters off toward the bathroom. She’s already forgotten to answer the question. Regardless, Dean admires the view as she walks away.

Dean hasn’t been dating Anna long, not even by his standards. He didn’t know much about her before either, except that she’d drawn the cover art for his friend’s debut album. He regrets now telling Sam he was bringing a serious girlfriend to his wedding. Especially since he hasn’t asked Anna, and again, they’d been together barely a month. He rubs the sleep out of his eyes and looks around on the floor for his jeans. Maybe ‘together’ is a bit strong, too. They’d been ‘hanging out and having sex pretty often’ for about a month. Dean hasn’t been with anyone else, but he doesn’t know about Anna. They’d never said if they were exclusive. He jumped around from relationship to relationship, sure, but he didn’t like to have more than one happening at a time. Picking up a one night stand seemed like a waste when you had a regular thing going, anyway. In any case, Sam was expecting him to show up to the wedding with a date.

Dean knew Sam felt a bit sorry for him. Sam had hit the jackpot, in Dean’s opinion. It was: go to college, find your future partner, get a job, and get married. Easy for Sam, not so much for Dean. Sam met Jess at Stanford and now they were getting married. Sam seemed to think it worked this way for everyone. _Some people want to enjoy their twenties, Sam_ , Dean thinks. Of course, Dean isn’t in his twenties anymore, as everyone so continuously pointed out. Thirty isn’t that old. Not too old to be single. Maybe Dean didn’t want to settle down and get married. _If I do, I have time,_ Dean thinks. _Thirty isn’t that old._ He tosses his jeans onto a pile of dirty clothes.

Dean is pulling his shirt over his head when Anna comes back. Still in her underwear, but hair brushed, teeth brushed, and looking more alert. Dean quirks a brow at her, hoping to remind her of his earlier question.

“So, Sam’s wedding,” says Anna. She grabs her clothes off of the floor. Dean watches her pull her jeans up over her hips before replying.

“Uh yeah. I kinda wondered if you would go with me,” he says. She looks over her shoulder at him, a bit surprised.

“Your brother’s wedding, though? You’re the best man,” she says. She glares at her rumpled shirt and slips it on. “Isn’t it a bit soon? We’re not even that serious.” Dean rubs the back of his neck.

“Right,” he says. “You’re right, uh – ”

“Look, Dean. You’re really sweet, I just… I don’t think I can be what you need,” says Anna. She buttons up the shirt and smoothes some of the wrinkles out. “We’re not in the same place.”

“What’re you talking about?” Dean asks. He just wants a date to the wedding. Anyway, he’d actually thought this thing with Anna was going well. It was new, sure, but, going well.

“I’m not looking for anything serious. I didn’t think the age difference would be a problem, but maybe you need someone who’s in the same place, you know, emotionally, as you.” Anna turns away again to look for her shoes. Dean stares at her. Age difference? He’s only three years older than her, he’s pretty sure. What is this stigma people have about being thirty?

“Sure,” he says, not sure at all. “So that’s a ‘no’ to going to the wedding? And also a ‘no’ for continuing whatever this is?” He gestures between them. Anna nods apologetically. She follows him when he wanders into the kitchen. “Okay,” he says. “That’s okay. Well…”

“I probably shouldn’t stick around for breakfast,” she says. She gives him a quick peck on the cheek before opening the apartment door. Dean half-smiles at her and walks her out.

“See you around, maybe,” he says. Anna waves and Dean watches her go down the stairs, arms crossed and leaning on the door frame, appearing much more casual than he feels.

He looks up at the sound of a door opening across the hallway. His neighbor, a man Dean has barely spoken to and who had just appeared wearing only boxers, reaches down for his newspaper and grins at Dean as he straightens up. Dean almost missed it since he was rather unabashedly checking the guy out. He drags his eyes away from the man’s chest at the sound of a voice from inside the apartment. His neighbor turns away then, closing the door behind him, leaving Dean flustered and momentarily forgetting about his breakup.

~*~

“Hey, Sam,” Dean says. He holds his cell phone up to his ear with his shoulder, leaving one hand on the wheel and one hand fiddling with the radio. Dealing with rush hour traffic in San Francisco was a bitch, but Dean was used to it by now. Monday morning seemed to be particularly awful, but that could just be down to it being Monday.

“Dean, you’re coming to the engagement party, right?” asks Sam.

“Wouldn’t miss it,” says Dean. “I should probably tell you I’m not uh bringing Anna to the party or the wedding or anything else.”

“Did you break up?” asks Sam.

“Looks like it,” says Dean. He braces himself for the emotional support Sam will no doubt offer.

“Are you okay?” asks Sam. “You can do better, anyway. She seemed flighty.”

“Flighty?” asks Dean, amused.

“Jess’s word,” explains Sam.

“Right. I guess she is,” he says. Jess had never even met Anna. “I’m over it. It wasn’t serious.” So Anna said. And it wasn’t, really. Dean was just feeling the pressure from his little brother getting married, his mom’s questions about his love life, the never ending string of 'okay' relationships that never went anywhere…

“You’re allowed to be upset about this, Dean,” says Sam. Dean rolls his eyes.

“It’s fine, Sam. I’m at work now, talk to you later.” He hangs up.

~

He can hear Bela Talbot through the glass doors of her office, tearing into a client who is looking ready to bolt. She can be scary, sometimes.

“Hot, though,” Charlie says, nodding at Dean. Oh, he’d said that last bit out loud. Dean cocks his head and smirks in agreement.

“Morning, Dean,” said Becky. She’s balancing a cardboard coffee holder, four coffees swaying precariously, and a pile of magazines. Dean reaches for the coffees to help her, earning a thankful smile in return. “Bela wants to see you in her office. Can you take those?” she asks. Dean raises his eyebrows at Charlie, who shrugs. He drops off the coffees at Bela’s desk after he’d goes inside.

“Winchester,” says Bela, enunciating each syllable in her pretentious accent. Or maybe it isn’t the accent itself, just everything Bela did that annoyed Dean. He takes a seat across from her without being asked. He waits for her to get on with it, crossing and uncrossing his legs. “Coffee?” she offers. It’s a fancy Starbucks brew with more sugar than he usually likes. “So, I’ll just get right down to it, shall I? We’re going to be making some changes around here.”

“Okay,” says Dean slowly. “What kind of changes?” He sips his overpriced coffee and watches her click her manicured nails on the desk.

“Cutbacks, mostly. We can’t afford to keep on everyone,” she says. She looks at him as she waits for her words to sink in.

“You’re firing me,” says Dean. Of course. What else could go wrong?

“Look, you don’t want to be in marketing, Dean. You’ve done a fine job, but is this what you want to do forever?” asks Bela. Her sympathetic smile doesn’t reach her eyes.

“I guess I won’t be either way,” he says. He shoves out of the chair and leaves the office before she can get another word in. A concerned looking Charlie is waiting at his desk.

“Fired,” says Dean simply. He begins piling up his few personal items into a box. He realizes he’d left the coffee in Bela’s office. It hadn’t been that bad.

“That blows, man,” she says consolingly. She helps him finish packing up and pats him on the shoulder. “Don’t be a stranger, Dean.” She points at him accusingly, as if he would let that happen. Charlie is the only real friend he’d made in this office.

“I’m not gonna let losing this shit job make me forget about you,” he says. Charlie hugs him before he leaves, and he doesn’t look back.

Once back at his apartment building, he sits in his car, delaying the inevitable walk up, which would make being fired all too real. He pulls his cardboard box into his lap and sorts through it. Mostly it’s full of paperclips and pens, and a few pictures of his family. Under a stack of semi-important papers is a women’s magazine addressed to Becky Rosen. “Must’ve grabbed this on accident…” Dean mumbles. A page is bookmarked and Dean flips to it, trying to waste more time. It’s one of those quizzes. “What’s your number?” The magazine is promoting an idea that it matters how many people a women slept with. Or, they are scaring women into thinking men care about that number and that if they want to ever get married, they should stop being such ‘sluts.’ Dean frowns at the national average of partners a woman had in her life – 10.5. A number he is way past. Not that he’s worried. This type of bullshit is just out there to make women feel bad about themselves. Too many lovers, too _few_ lovers… He scoffs at the rest of the magazine. Although, some of it isn’t bad – a couple of good recipes, a cute article about cats that _no one_ must know he liked.

How many partners _had_ he had, though? He doesn’t think it could be more than twenty, or forty. That wasn’t bad, right? He shakes his head. It doesn’t matter, _obviously_.

He can hear music from inside his neighbor’s apartment as he’s unlocking his door. Good, live music. He looks back across the hall, growing more curious about the guy in 6A.

~*~

After a full week spent doing nothing but watching television and searching the internet halfheartedly for a new job, Dean gets dressed up and drives out to his mom’s house for the engagement party. The wedding is only a couple months away, but the Campbells always like to put on a big show. Dean thinks Mary is trying to show off for Jess’s family, and distract herself from the news that John is bringing a date to the wedding. It still seems too soon to Dean for his dad to be bringing a strange woman to his son’s wedding, even though his parents have been divorced for over a year now.

Dean parks his Impala in the garage to save her from being dinged up by rowdy party guests. By the number of cars parked in the drive, it seems like most of his family is already here and Dean plans to avoid _all_ of them if possible.

Inside, Dean manages to squeeze past a crowd of people he doesn’t recognize that are probably Jess’s friends or family, and make it upstairs to a guest room. Sam’s inside already, hiding out and holding his phone, but ignoring the pings of new messages. He’s taken the only chair in the room – an overstuffed, ostentatious thing.

“Looks like we had the same idea,” says Dean, sitting on a bed piled high with pillows and throw blankets.

“I needed a break,” says Sam. “Mom invited a lot of people to this thing. She knows the wedding is soon, right? We’ll just be dragging everyone back out in a couple months for that.”

“Mom wants to do something. You know, Jess’s parents are paying for most of the wedding stuff, and she wants to show she can throw a party, too.” Mary calls Dean often to talk about this, since he’s much less busy than Sam these days. Dean tries to get comfortable sitting on this huge marshmallow of a bed, but it’s proving difficult.

Sam shakes his head, too long hair flopping all over his face. “Kinda wish we’d waited a bit on the wedding. I thought a year was long enough after the divorce, but there’s still so much _drama_ …”

“Mom isn’t used to an empty house,” says Dean. “No one to take care of.”

“No one to take care of, right.” Sam laughs. “We may be grown up and out of the house, but I don’t think anything short of moving across the country will stop Mom from trying to take care of us.”

“She’s lonely.” Dean shrugs. “She’s latched on to us with Dad gone, especially with his new girlfriend.” Sam nods in agreement, but is unable to answer when Jess shows up in the doorway.

“I thought I might find you up here,” she says, sounding exasperated and unsurprised by Dean’s presence. “And Dean, too. I heard about Anna, are you doing okay?” Jess, sweet as ever, blonde curls carefully styled, manages to transition from annoyance at Sam to concern for Dean in an instant.

“Yeah, I mean, I’m unemployed and single, but other than that, couldn’t be better.”

“Wait, unemployed?” asks Sam, nearly dropping his precious smartphone in his surprise.

“Forgot to mention it.” On purpose. “I was ‘let go’ from my job on Monday,” Dean explains.

“What are you going to do?” asks Jess.

“Not a clue,” says Dean. “I’ll figure something out.”

“I’m not worried about you, man,” says Sam. He pats him on the shoulder as he stands up, towering over everyone once again. “You always bounce back.”

“Yeah, well. Wasn’t too attached to that job anyway,” says Dean. Getting off the bed is a challenge and he falls deeper into it when he tries to stand. Both Sam and Jess are laughing, so Dean just lays back against the pillows, fighting to keep a grin off his face for dramatic effect. “Just leave me here, there’s no use for it.”

Downstairs, nobody seems to have noticed their absence. Dean’s absence, at least. Sam and Jess get swept away into the living room as soon as they make it to the last step. Dean is able to sneak away to the kitchen and fill up on snacks and the fancy cocktails Mary must’ve had made. He is immediately inclined to find the bartender that must surely be around somewhere, and make friends with him. If he learned anything from his father, he learned this – drink away the pain.

Later, once Dean has had more than his fair share of alcohol for the evening, Mary calls him up to make a toast to Sam and Jess.

Everyone seems to be standing very close together and the furniture is not where Dean expects, but somehow, he makes it to the middle of the room and clinks his glass, nearly empty but enough to toast with.

“To Sam and Jess!” says Dean. The guests hold up their glasses at Dean’s words and share confused glances until Dean realizes his mistake. “Wait, there’s more! Remember when Sam started dating Jess, first time I met her I told him, ‘She’s way out of your league, brother,’ no that’s not it, I told Jess, ‘You are completely outta my brother’s league.’ Anyway, the point still stands.” Some people laugh awkwardly, others are still holding their glasses up, hands wavering a bit. It’s Sam’s turn to be exasperated. Jess looks like she’s holding back a laugh. “They were great together, but maybe they started dating too soon, because they broke up for a while, there. Was it a year, two? When they got _back_ together, they were better than ever. Which really goes to show how important it is to give people second chances.” Dean smiles. “When you love someone, uh, when you are in love with someone and they, too, are in love with you, uh – you can always come back to each other. So, to Sam and Jess and their happy ending,” Dean finishes, unable to keep from waggling his eyebrows suggestively at the couple, earning a disappointed (amused, Dean likes to think) look from his mother. Everyone raises their glasses and drinks.

Mary takes Dean’s glass away before his can finish it off. “I think you’ve had enough.”

~

“I’ll get another round of shots,” says Dean. The girls around the table cheer, already a little too drunk perhaps for another round, but not if Dean’s buying. Somehow, Jess’s friends had convinced Dean to go to a bar with them after the party ended. Dean had even invited Charlie along, and she was having an even better time than he was with Jess’s former college roommate, Gilda. Sam was back at the house, playing poker with his friends. _Why_ Dean was here, he had no idea, and he was especially regretting tagging along when he spotted Bela at the bar. He tried to order his round discretely, but he was loud when he was drunk, and Bela was sitting closer than he’d thought.

“Fancy seeing you here, Winchester,” she said, looking up at him with eyes a cooler shade of green than his own. Her voice was as smooth as ever, unaffected by the tall glass of wine in front of her.

“Well, I’ve got nowhere else to be now,” he says. He tries to ignore her in favor of taking the tray of shots, but she stops him with a hand on his arm.

“Let me pay for that,” she says. “I feel terrible about letting you go.”

“Firing me, you mean,” he says, tonelessly.

“Bit harsh, isn’t it? The decision came from higher up, it wasn’t my place to question it. Someone had to go,” she says.

“Can’t expect me to feel good about it,” he says.

“I think I can make you feel _very_ good, Dean,” she says. Her eyes light up in a way that is, frankly, a little scary.

Dean takes the tray and shuffles back a few steps. “Thanks for the, uh, shots,” he says. He means to make a quick escape, but is stopped by the large mass of people waiting to get to the bar. Bela doesn’t follow him to the girls’ table, though, and he can breathe easy.

Shots are passed around, and Charlie is more or less sitting in Gilda’s lap by this point. The rest of the girls are loud and giggly, and Dean’s bad mood from the last week is slipping away at last. Beside Jess is a girl named Meg, wearing dark red lipstick and looking smug about something. Dean thinks the girl beside her is Sarah Blake, and beside her is Dean and Sam’s childhood friend Jo, who’d hit it off with Jess immediately after they met.

“It’s sort of a miracle, isn’t it Dean? That you haven’t slept with any of us here,” says Jo, smirking.

“Oh, c’mon, Jo.” He rolls his eyes, but decides to humor her. “You know I would have sex with any one of you if you asked. Though, I don’t think Charlie would be into it.” Charlie doesn't catch his smile, preoccupied as she is.

“ _Jess_ wouldn’t be into it,” says Jess, scoldingly.

“Right, Jess is off limits now, guys,” agrees Dean. “So threesome? Or what do you call it when it’s four people? I guess foursome,” he says, looking meaningfully at Jo, Meg, and Sarah.

“Shut up, Dean, we’re single, we’re not desperate,” says Meg.

“You would be glad to have me! I get rave reviews,” he says.

“How many women _have_ you been with, Dean?” asks Meg.

“Don’t forget the men,” says Charlie.

“It’s quite an impressive list, I’m sure,” says Jess.

“It’s not as many as you think,” says Dean. “Although, I’m not _sure_ of the number.”

“If you don’t know the number, it’s too high,” says Sarah.

“I don’t see how it matters,” says Dean.

“Don’t you want to settle down sometime?” asks Jo.

“Sure, I guess. But what better way than sleeping with as many willing individuals as possible to find the right one?”

“I think there are better ways, Dean,” says Jo.

“Let’s leave him alone, you know he’s just getting over a breakup,” says Jess. Dean glares at her, but it’s too late. He is overcome with condolences and apologies for nothing from the others.

Dean buys himself another shot.

~*~

Looking back, the final shot was probably a mistake.

He wakes up to the sun, too bright in his eyes, and a mouthful of brown hair. His eyes widen, and he’s almost afraid to see who’s in his bed. If it’s _Meg_ …. Shudder. He supposes it could be Sarah. What he is not expecting to find when he gets up is Bela Talbot sprawled naked in his bed. He falls out of the bed in shock, hitting his ass painfully on the wooden floor he thought had been a good idea at the time. Wood floors in a bedroom, the nerve of some people.

Thankfully, he is wearing underwear at least. It’s possible they _didn’t_ have sex, but Dean is ninety-nine percent sure they did. He groans loudly from his spot on the floor, which seems to wake Bela up. He finds a shirt hurriedly to spare himself some dignity, but already hope is lost. Bela sits up and stretches in all her glory and Dean hates himself for looking. Without talking to her, he goes to the bathroom to take care of business and comes back before she’s fully dressed.

“Can you zip this?” asks Bela, after pulling on the black dress she’d worn last night. Dean sighs in resignation. Will his humiliation never end? He does zip her up, though. He also hurries her out of his bedroom and into the living room with a hand on her back.

“Well, I’m sure that was fun, but you should probably – ” he says, or starts to say, but before he can get the door open, it opens from outside and in walks his handsome neighbor. Again with the boxers, man. Dean and Bela both admire him before Dean is able to speak again. The guy shuts the door quickly and suddenly seems to realize the apartment he’s burst into is inhabited.

“Hello, uh,  Dean?” says the guy. He seems a bit too unsure for a guy running around in boxers, in Dean’s opinion.

Dean stares blankly at him. It’s not fair that this guy knows his name somehow already. “Hey,” he says. “Uh, look Bela. You should probably go, I’ve gotta talk to, um, him about some stuff.” Convincing, Winchester, way to go.

“Of course,” says Bela, looking between both men skeptically. “If you want to do it again sometime, you know where to find me,” she says.

“Yeah, yeah, sure,” says Dean. He all but pushes her out the door once he gets it open again, then slumps against it once it’s shut. “Thanks, man.” The other guy gives him a tiny smile, eyes crinkling, and damn are they _blue_. “What’s your name again?”

“Sorry, I wasn’t even sure if yours was Dean. Is it?” Dean nods. “I’m Castiel,” he says. Castiel holds out a hand to shake, which Dean takes, feeling only a little awkward about shaking hands with a handsome half-naked man in his living room while he, himself, is only in boxers and t-shirt.

“Cool name, Castiel,” says Dean. “So what’re you doing here?”

“Right, well, I had a similar sort of problem,” he says, sheepishly.

“Sneaking out on a hookup?” asks Dean.

“Basically,” agrees Castiel. “I find it easier than talking to them in the morning.”

“I hear ya,” says Dean. He’s finding it hard to pay attention with so much exposed skin on display. Castiel doesn’t seem to notice Dean’s problem.

“I saw your speech on YouTube this morning,” says Castiel.

“You saw my what on where now?” asks Dean.

“You were very drunk, I’m sure you don’t remember. You went to a bar last night, right? You gave a lengthy speech about love and sex and, I don’t know, it rambled,” he explains.

“Someone took a video last night and posted it online? And you’ve already seen it?” asks Dean. Castiel motions Dean over to his laptop, which is already on, so he has no trouble pulling up the offending video. Dean watches it, leaning over Castiel's shoulder with his mouth hanging open. “How did you know about this already?” That one point is sticking out to him. Castiel looks a bit flustered now.

“I have all the residents on Google Alert,” he says. “I find it’s best to know what my neighbors get up to. I’m not a creep, by the way. Just a concerned citizen. And a private investigator.”

“You have me on Google Alert,” says Dean, slowly. “So, you did know my name.”

“Yes, I lied about that. Thought it’d be less weird if I said I wasn’t sure,” he says, eyes twinkling.

“Right.” Dean laughs. Castiel is nothing like he’d expected. “Still weird, but you seem like a decent enough guy. Aside from the ‘keeping tabs on the neighbors’ thing and the ‘walking into stranger’s apartments half naked’ thing.” Dean pats him on the shoulder, his smooth, bare shoulder. On pulling away, he thinks he probably kept his hand there a second too long.

They can hear a door open and close across the hall. The walls in this building are alarmingly thin.

“That’s my cue,” says Castiel, standing. “Sorry about the – all of that,” he says.

“No problem,” says Dean. “Anytime you need to hide out, feel free to barge in uninvited.” Dean grins at Castiel, who rolls his eyes.

“I’ll hold you to that,” he says. 

"Hey, should a private investigator really be breaking into apartments, anyway?" asks Dean. 

"I'm not a cop, Dean," says Castiel, amused. And then he’s out the door. Dean is left staring after him, wondering what the hell his life has become.

**Notes for the Chapter:**

> thanks for reading! this is my first destiel fic and also my first shot at writing fanfic again in several years, so go easy on me. ;) and apologies for any typos or grammatical errors. 
> 
> btw trying to make Dean work as Anna Faris's character is not easy haha so expect plenty of diversions from the movie.
> 
> also, if you want, follow me on [tumblr.](http://galadreel.tumblr.com)


	2. Chapter 2

“Why am I here, exactly?”

“You like cake, right?” asks Sam.

“It’s pie. Pie is what I like,” explains Dean. It’s like they’d never met.

“Whatever. You like food, though.”

“You say that like there are people who don’t like food.”

“C’mon, Dean, you like to eat, you like dessert. Pie, cake, who cares?”

“But why am _I_ at your cake tasting and not Jess?”

“Jess couldn’t get out of work, and we already had the appointment booked. She said I should use it to pick out my groom’s cake flavor. We’re coming back next week to get her cake.”

On the table in front of Sam and Dean is a wide variety of wedding cake, that, frankly, all look delicious to Dean. Any of them would be fine, he’s sure, but just to check, he takes a bite of each of the three in front of him.

“Wow, tough life,” says Dean around a mouthful of cake. “Wait, how many cakes are you getting?”

“Just the two. She wants me to have something for _me_ at the wedding, since most of it’s for her, but that’s fine really I - ”

Sam probably finished that sentence, but between eating more cake and the sound of people walking in the door, Dean misses it. The new arrival looks awfully familiar…

“Holy shit, that’s Benny,” says Dean, eyes wide.

“Who’s Benny?” asks Sam. Dean stares at him. Shit.

“I never told you about Benny, huh?”

“I don’t think so.” Sam glances back behind him where Benny is looking at the cake display.

“We were a thing. It was before I told you about me.” Sam frowns at him.

“So you dated, but it was before you came out as bisexual,” he corrects.

“Yes, yes that.” Dean looks over Sam’s shoulder. “It was years ago, back when you were in school and I was living in LA. He looks a little different though… The beard! He used to have this thick beard, and he refused to shave it. Guess he got over it.”

“Go talk to him,” Sam suggests.

“Uh, sure, no I can do that, yeah.” He pushes his chair back from the table and stands up quickly. Almost too quickly, as he nearly falls over.

“I have faith in you, Dean.” Sam smirks. Dean waves him off.

“Benny, hey,” he says once he reaches the counter.

“Hey, brother,” says Benny, turning around. Dean had caught himself thinking of that drawl in moments of weakness, and here it was, live and in color. Or, sound. “Fancy seeing you here.”

Dean gestures over at Sam. “Yeah, well, I’m just here with -”

“Congratulations, then. Gettin’ married, huh? Me too,” he says before Dean can finish.

“What? Uh, sure,” says Dean, because getting caught in a tangle of lies is infinitely better than admitting to an ex that you are, in fact, single and just tasting cake for your brother’s wedding. “Who’s the lucky, uh, person, then?”

“She’s around here, somewhere… Andrea, c’mere and meet an old friend o’ mine.” Andrea turns out to be a beautiful woman with a long braid of thick brown hair. “This is my fiancée, Andrea Kormos.” To Andrea, he says, “This is my old friend, Dean.” By the confused look on Andrea’s face, Dean must grimace, rather than smile, at her at the shock of being called just a “friend.” Dean doesn’t know what Benny does with his other friends, but if it’s anything like what they used to do, Andrea should probably be concerned. Although he’s sure Benny’s never looked at him the way he’s looking at her.

“Good to meet you, Andrea,” he says, summoning every bit of politeness he has. “And good seeing you again, Benny.” Dean is out of there and sitting next to Sam again before he can embarrass himself any further.

“So?” asks Sam. He’s still sampling the cakes on the table, but instead of eating half of each slice like Dean, he takes a more reasonable single bite.

“He’s good. Got a fiancée.” Dean reaches for an untouched slice of chocolate cake with chocolate frosting. “This is delicious,” he says, pointing at the cake exaggeratedly.

“Tell me what he said.” Sam knows him better than Dean realizes sometimes.

“He thinks we’re getting married.” Sam stares, then spontaneously bursts into laughter.

“Pretty sure that’s not legal,” he says, almost crying from laughing.

“What, marrying your brother? No, I don’t think so.” Dean’s grin fades when he continues, “He told her I was an ‘old friend.’”

“Shit. Sorry, Dean. Do you think she knows that he’s interested in men?”

“Probably not, or he’d own up to our relationship or whatever. I’m a catch.” He’s back to grinning, even more cockily if possible. Sam sees right through it and looks at him with a touch of pity. He’s surprised how much it hurt to see Benny again, and happily engaged to someone else. From his single second interaction with the couple, he could tell Benny was head over heels. Dean had been happy with Benny, sure. But he knew now why it hadn’t lasted. He thinks, maybe, it’s possible that what had hurt was seeing Benny look at Andrea with complete and utter _love_ , and realizing that he had never looked at anyone like that before.

~*~

For lack of anything better to do, and with the job search turning up nothing, Dean takes to the internet. His apartment is growing messier the longer he's unemployed. Dishes piled up in the sink and boxes of take out on his desk and his table needed to be thrown in the trash, but Dean is too busy being bored to actually clean anything. He finds the YouTube video that had made him “famous” and watches it again, cringing. He decides he needs to find out who posted the thing, just for his own peace of mind, so he begins his search. Five minutes later he discovers that the poster of the video – “bornunderabadsign” – is Jess’s friend, Meg Masters. “I knew she was shifty!” he says to his empty apartment. He opens Facebook, for probably the first time since he signed up for it, and looks her up to leave an angry message about posting videos of drunk acquaintances embarrassing themselves on the internet without their permission, and how you should _not_ do that.

On Meg’s page, Dean spots his old girlfriend Lydia on her friends list. “Figures they would be friends…” Crazy or not, she does look nice in her profile picture. It’s possible some of his other exes have gotten better with time. Benny looked great and was settling down. It might not be a bad idea to look up his exes and see if any of them were worth a second shot, or thought _he_ was worth a second shot. Lydia and Benny were out of the question. But Carmen or Cassie might be okay… or Lisa. Dean had nearly forgotten about Lisa Braeden. It had been ages since he’d seen her, nearly ten years now. He jots down a list of notable exes on a piece of notebook paper and stares at it. How could he find them? Facebook is certainly an option, but he’s not sure he wants to reconnect via the internet. He doesn’t want them to think he’s just looking for a hookup.

He decides he should get out of the apartment and get something to eat before thinking any more on this. In the hallway, he runs into his neighbor again, fully clothed this time. “Hey, Cas,” says Dean, before locking his door behind him. “Where’re you off to?”

“Work,” he says simply.

“Oh yeah, private investigator.” An idea, maybe a dumb idea, but still, comes to Dean. “You can find people pretty easily, right? Do you think you could find some people for me? I swear it’s not creepy.”

“I can find anyone, usually,” says Cas, squinty eyes looking right at home on his face.

“I’ve got a list I can give to you. I can’t really _pay_ you, but I’ll let you use my apartment to hide in, or whatever.”

“That works, Dean.” He grins. “Give me the list and I’ll get started.” Dean ducks inside his apartment, quickly, and returns with the list. Cas’s eyebrows raise as he glances over it. “What is this?”

Dean lowers his eyes and answers, “Just a, uh, list of my exes.” Cas is outright laughing now.

“Okay, I’m not going to ask any more about this. I’ll have something for you soon.” He’s still chuckling as he heads down the stairs, and Dean hesitates a bit before following him to avoid having to explain himself further. He decides to call Charlie to meet him at the sandwich place they used to frequent on their lunch breaks, and heads there straightaway after she agrees.

“Dean-o! This place is not the same without you,” say Charlie, tossing her bag onto the floor by her chair as she sits down across from Dean.

“You’ve been coming here without me? I can’t believe I’m hearing this.”

“Should I find a new set of restaurants to go to on my break?”

“That’s exactly what I expected you to do.” Dean smirks. A waiter comes by to get their drinks order. A beer for Dean, sweet tea for Charlie.

“We don’t have time for this, dork. I only have an hour, so spill. What have you been doing with all your new free time?”

“I didn’t choose to have all this free time. I haven’t been doing much of anything, except looking for another job. I _have_ been helping Sam with wedding stuff, some. Hey, I told you about Benny, right?”

“Chewbacca, of course,” says Charlie. As far as comparisons go, it’s not too far off.

“Well, I ran into him at the bakery me and Sam went to.”

“Was it awkward?”

“Yeah, actually, he was there with his fiancée – ”

“Okay, I can’t wait anymore. What the hell happened with Bela?” blurts Charlie.

Dean nearly chokes on the first sip of his beer. “What did you hear?” he asks warily.

“Nothing, but I saw you go off with her at the bar,” she explains.

“Why didn’t you stop me? Fuck,” he says.

“I wasn’t any less drunk than you. What happened?”

“I’m not entirely sure. You know, I don’t even know how I got that drunk, I thought I was immune.”

“You’d been drinking since before the bar, though.”

“Good point. All I know is when I woke up, Bela was naked in my bed.” Dean shakes his head. “Drunk or not, I don’t understand how that happened. She hates me. And I don’t think the other night improved our ‘relationship.’” He puts air quotes around the word, mostly because it annoys Charlie.

“Dude, I can’t believe you slept with our boss,” says Charlie, and she almost sounds impressed.

“Not _my_ boss,” he says.

“Touché,” she agrees.

“I’ve been thinking, after that disaster and seeing Benny… I need to start taking things more seriously. I think I was looking for that with Anna, but it wasn’t what she wanted, so maybe… I’ve got my neighbor looking up my exes for me. I don’t think I gave all of them a fair chance the first time around.” Dean looks to Charlie for her opinion, but is saved by the waiter, who is back to take their order. As soon as he leaves, she rounds on him.

“You think that’s really a good idea? Didn’t you break up with these people for a reason?” she asks. “And what neighbor?”

“You know how hard it is to meet people, Charlie. At least I know something about them already, and we worked together at some point… It’s not the best idea I’ve ever had, I’ll admit.” And it isn’t, but it isn’t _that_ bad, either. Sometimes people get back together, right? “My neighbor, Castiel. He’s a private investigator, or he says he is.”

“Castiel? Unique,” she says approvingly.

“Yeah, he’s cool, though.” Dean’s phone dings, alerting him to a new text. “Speak of the devil.”

“The mysterious Castiel?”

“Yep, he says he’s got info about Carmen and to meet him at this club later.”

“Why’re you smiling?”

“What? I’m not smiling.” He is.

“You are! Excited to see Carmen?” she asks, poking him enthusiastically.

“Uh, sure. It’s been a while.” Luckily, she didn’t think to ask if he was smiling because of Cas. Which he totally wasn’t. If Charlie catches a whiff of even the _tiniest_ crush she becomes Cher Horowitz. “So! How’s Gilda?”

~*~

The club Cas texted about is in one of the more popular neighborhoods in the city, at least if the traffic getting there is any indication. Dean parks as close as he can and squeezes his way through the crowd of people to where he can see Cas sitting at a booth. He slides in across from him and Cas passes him a beer.

“I wasn’t sure what you liked,” he says.

“Not a very good detective are you?” Dean laughs at Cas’s blank stare. “Beer’s beer, man. This one’s great, thanks,” says Dean, taking a sip to prove his point. “What are we doing here?”

“Carmen Porter works here.” He gestures toward the bar where a dark haired girl is pouring drinks. “She also does some modeling on the side.”

“Huh. That’s what she was doing when we were together. I thought she was going to nursing school?” Dean looks between the people standing around to catch another glimpse of her.

“I didn’t find anything about that,” says Cas. “Are you going to talk to her?”

“We broke up because she was really into partying and that’s not me… I was hoping she’d moved past all that, become a nurse like she wanted. Grown up.” He looks at the stains on the table, the initials carved into the wood, thinks about if he’d like to see ‘D+C’ in a crudely drawn heart. ‘C’ for Carmen, obviously. “I don’t know if I want to go back to the same relationship.”

“Time changes people. For better or worse,” Cas says sagely.

“Deep,” Dean quips. “Time didn’t do its job on her, though.”

“Perhaps she’s happy where she is,” he says.

“You’re right, she should do what she wants without me getting in the way.” Dean looks at Cas, then, assessing his face up close like he’s been unable to do before. He’s basically a stranger, but Dean finds it incredibly easy to talk to him. Maybe it’s the honest expression in his eyes, or the kindness he’s already shown Dean.

“Dean?” Oops, he’s staring.

“Uh yeah. Sorry, this was a bust, Cas.” He fiddles with the paper on his beer bottle, pulling at the wet label.

“It’s no problem. We should finish our drinks, at least.”

“’Course. Hey, tell me about yourself. You know an uncomfortable amount about me, already.” Dean takes a hearty swig of beer. “Castiel’s a pretty unusual name. What’s it mean?”

“On the contrary, Dean, I don’t know much about you at all. A list of exes is hardly revealing. If you must know, though, Castiel is an angel’s name. Or so my parents said. They were very religious. My siblings got the “ordinary” biblical names.” Dean smiles when Cas air quotes the word. “I have a brother, Gabriel, and a sister, Hannah.” The corner of Castiel’s mouth turns down a bit, the weary expression of a kid-turned-adult stuck with a funny sounding name for life.

“It suits you. It’d be _weird_ if your name was Tyler or Jake.” Dean grins. “Religious, though? You don’t strike me as the type.”

Cas says, “My family and I had a falling out. I didn’t hold some of their same beliefs, so I gave it up altogether,” and no more.

“I can understand that, my family has never been a Rockwell painting.”

“Is your family religious, too?”

“Oh, hell no. My mom and brother a little more than me and my Dad, but not really. We never did the church every Sunday thing.” Dean remembers a lot of Sundays playing games with Sam and eating homemade apple pie. He remembers his parents fighting too, when John would wake up late in the morning after drinking too much the night before.

“Are you close with your brother?” Dean wonders briefly how Cas managed to turn this back around on him, then remembers the guy’s job.

“We are, yeah. He’s getting married soon. That’s what this whole thing’s about, actually,” explains Dean.

“Ah, you need a date to the wedding.”

“Right in one. _I_ ’d be okay with going alone, but my family would be insufferable.” Dean rolls his eyes. He can imagine the remarks from the Campbells, and how his mom would hide her disappointment about his breakup with that ‘nice girl, Anna.’ He also wouldn’t mind having a date to hide behind as a shield so he can avoid his dad and his new girlfriend. “You close with your siblings?”

“Not as much, now. I moved across the country to avoid them all. But we talk on the phone occasionally and I go back for holidays,” he says.

“Where’s home for you?”

“Small town Illinois,” says Cas, although without a trace of a Midwestern accent.

“You don’t sound like it,” says Dean.

“That’s on purpose,” he says. “Where are you from?”

“You don’t buy I’m from California?” Dean is growing rather fond of Cas’s exasperated expression, and being the one to put it there. “I’m from Kansas.”

“You _do_ sound like it.”

“It’s hard to shake,” says Dean. “You must have more persistence than me.”

“I do,” Cas says easily.

**Notes for the Chapter:**

> the next chapter should be much longer! thanks for reading <3


	3. Chapter 3

“Quite a list you’ve got here,” says Cas, swiveling around in his desk chair. 

“Yeah? I didn’t write them all there. The real thing’s actually not as long as I thought, only nineteen.” Still a respectable guy, at least according to _Cosmo_. “How long’s yours?” After the club, and Dean’s disinterest in reuniting with Carmen, they’d gone back to their apartment building, but somehow Dean had ended up across the hall at Cas’s. Dean wonders if this whole thing is a mistake. Carmen looked as good as ever and seemed to be doing fine. Dean had been into her when they’d dated, and it’s not like he was looking for anything too serious, just a date. Right? But he couldn’t bring himself to go talk to her, to restart what had been a mediocre relationship at best. Maybe he should narrow his list down to the few he actually _wanted_ to see again. Someone he could see himself with, potentially long term, for once.

“My list?”

“Well, I wasn’t asking about your dick,” Dean counters easily. He pauses and stares at Cas, eyes wide. Cas is looking back, corners of his mouth twitching. He doesn’t manage to hold back his laugh. Dean doesn’t know why he’s so flustered by a joke he’s made a thousand times.

“Oh, I don’t keep count.”

Dean raises an eyebrow. “That many, huh?” Cas shrugs in response. Dean is surprised, and yet not, by him. He’s good looking enough for all the sex he seems to be having, but he doesn’t strike Dean as the kind of guy to seek out hookups. Or manage to smooth talk his way into one. “How does that work anyway?” he asks.

“What?” Cas is typing at his computer now, sure fingers flying over the keys. Dean is momentarily impressed by his computer prowess, then notices the guy is on Facebook.

“You bring a lot of people back to your apartment,” says Dean.

“And?” Cas does not seem impressed with where this is going.

“I guess I was just wondering how you do it,” he says.

“How do _you_?” he returns, narrowing his eyes.

“Um, I don’t, really.”

“There was a woman in your apartment the other morning,” Cas points out. As if Dean’s forgotten _that_ whole incident.

“True. She was my boss. Drunken mistake,” he explains.

“Did she fire you because the sex was bad?” Dean is not entirely sure he’s kidding. Cas’s poker face is next level. Despite himself, the tips of his ears turn pink.

“I’ll have you know I was fired several days _before_ the sex, _and_ I’m sure it was not _bad_ , although I can’t say one hundred percent, because I don’t exactly remember it.” Cas bursts out laughing, and Dean smiles reflexively upon hearing it. “But that kind of thing doesn’t happen a lot. I’m more of a – what do they call it? Serial monogamist.”

“I can tell from your list. I’m the opposite,” says Cas. “Although I don’t discriminate based on gender, either. And to answer your earlier question, a majority of the people I bring home, I meet at shows.” He nods towards a guitar across the room that Dean had glanced at, but not noticed properly.

“You’re in a band? Aren’t you a detective?”

“I have time off, sometimes. And _private investigator_.”

“So, private investigator who plays guitar in a band and talks like a text book?”

“Text book?” Cas laughs, and Dean shrugs. “I just read a lot.”

“Busy man,” says Dean.

“Not as busy as all that,” he says. “I don’t have much of a social life, or not outside of the band. But then, I don’t spend a lot of time just hanging out with those guys, either.”

“Don’t worry, man. I have zero social life.”

“Really? That surprises me.”

“Because I’m so charming and attractive?”

“Because your head is so big, I expect everyone gravitates to you,” Cas deadpans.

It’s Dean’s turn to toss his head back in laughter.

“But, seriously - is there a difference between a detective and a private investigator?” Dean asks once he’s calmed down.

“A detective usually works for the police department. I work for an agency, and I’m not a cop,” he says with the boredom and familiarity of someone who gets asked this question often.

“Right. So, you find people through what, Facebook?”

Cas rolls his eyes dramatically. “Your people aren’t that hard to find, you’re just terrible at using the internet, apparently,” he says.

Dean points a finger at him. “Hey, none of that. And if they’re so easy to find, why haven’t you found them all yet? Maybe I don’t even need you for this. I found Benny all on my own, bumped into him actually. And I thought he lived in LA, so I’m not even sure why he’s in town.”

“Benny’s not on your list,” says Cas, double checking the crumpled paper.

“Nah, he’s getting married.” Dean gets up from his spot on the couch to peer over Cas’s shoulder at the list. “Have you looked into Lisa Braeden?”

“Not yet. She’s the famous fitness instructor in LA, right? Famous people are difficult to in contact with.”

“That makes sense. I haven’t talked to her in years… We were friends when we were kids and dated in high school and for a couple years after that. Probably my longest relationship, actually,” muses Dean. It’s no wonder he stills thinks about her sometimes.

“I’ll keep trying, Dean. I just found Cassie Robinson, though. Recently divorced,” he says. “She’s selling her house, so you could go check it out, happen to see her there.”

“That’s not a bad idea. She’s great, actually. I don’t know how happy she’d be to see me, but it has been a few years, so. You wanna check out the open house with me?” Dean doesn’t want to show up alone, especially if it goes badly.

“I’ll go with you,” says Cas. “I might have to reschedule my reading, though.”

Dean pushes his shoulder playfully. “Dork.” Cas grins and swivels back around in his chair to face him. He suddenly seems much too close and Dean takes a small step back. “Well, when you get around to it, you should find Lisa. Best sex I’ve ever had.” Dean winks his obligatory man’s man wink.

“You haven’t had sex with me,” Cas says. Again, so seriously it takes Dean a second to catch up. Cas’s smirk is so distracting, Dean can’t figure out a witty response. Of course, now all he can think about is what sex would be like with Cas. Cas is about as tall and as strong as him, and Dean’s seen him nearly naked already, so it’s easy to picture him spread out on his bed, hair somehow even messier, skin flushed and sweaty… He’s taken too long. Dean feels the return of his blush.

“Um, no I haven’t,” he says, not as wittily as he was hoping for. Cas’s smile becomes more genuine, and Dean finds himself returning it again before he clears his throat. “Text me about the open house and we’ll go together. I’ll, uh, see you then. It’s getting late.”

“Right. Goodnight, Dean.” Dean feels his eyes on his back as he walks to the door, and tosses a “’Night, Cas,” back at him without looking.

~*~

“Dude, this place has the best burgers,” Dean says excitedly. He backs into the small restaurant, grinning at Cas’s hesitant expression.

“I’ll trust your judgment,” he says. “I do love burgers.”

“It’s not just a burger. It’s a treasure,” assures Dean. “It’s nice to eat burgers again.”

“When did you stop?” asks Cas.

“My last girlfriend was vegan, so I tried to be supportive. Ate some veggie burgers. Not bad, actually,” he says. “Don’t tell anyone I said that.” They wait in the short line and order their food to-go.

“Honestly, I was expecting a meat-related joke,” says Cas.

“Like a meat is code for dick joke?” asks Dean.

“Just based on what I know of your personality so far, yes.”

“Sorry to have disappointed, man,” says Dean. They get sodas and grab their burgers on the way out. Dean skipped breakfast that morning, since he only woke up ten minutes before Cas showed up at his apartment, so he takes a huge bite of his burger as soon as he gets it out of the bag and unwraps the paper. “What d’ya think?” he asks Cas, mouth full.

“That’s disgusting,” he says.

“The burger?!” asks Dean, nearly spitting bits of food on Cas in his surprise.

“No, _you_ ,” says Cas. “This burger is the best thing I’ve ever had in my mouth.”

Dean, never one to miss a setup like that, says, “I bet I can find you something better to put in your mouth.”

“There it is,” says Cas. Dean pats his back and takes another huge bite out of his burger. He faces Cas, walking backwards, arms spread wide.

“What can I say, everyone’s a thirteen year old boy at heart. And what’d I tell you about the burger, huh?”

“I believed you,” he says.

“Ah, you were skeptical,” says Dean.

“I thought you were overselling.”

“Yeah, well, now you know to take my word as the gospel truth,” he says.

“Let’s just go to the open house, Dean,” says Cas, pushing Dean’s shoulder to get him to walk facing forward.

*

They end up at a street full of the kind of Victorian style row houses that San Francisco is famous for. The whole area is beautiful and full of parents with their kids, tourists, and dogs. Dean can make out the Golden Gate Bridge in the distance.

“Holy shit,” he says. “Think we’ll run into Uncle Jesse?” he asks Cas, winking. “Dibs.”

“I don’t think John Stamos actually lives around here,” says Cas seriously.

“Don’t crush my dreams, man,” he says. “Is this it?” Dean gestures to a house down the street with the door hanging open.

“It must be, who else would leave the door open like that?” Cas follows Dean inside the house, which is just as beautiful inside as it is outside.

“Dude, who can even afford to live here? It must cost a fortune…”

“I don’t know, but I’m going to use their fancy restroom while we’re here.” Cas runs upstairs to find a bathroom and leaves Dean in the entry. Tall windows let in enough natural light to render electric lights useless during the day, and the modern furniture decorating the living room is straight off a home renovation show. Dean admires the original painting decorating the wall above the fireplace, which draws his eyes to the family photos and birthday cards on the mantle.

“Oh, fuck,” he says. The man in the fisherman’s hat may not have a beard anymore, but it is undoubtedly a picture of Benny and his soon-to-be wife, Andrea, on a boat. Is this some elaborate prank of Cas’s to trick him into seeing Benny again? That sounds more than a little ridiculous. What are the odds that Benny would live anywhere near Cassie? And what kind of idiot just leaves their door wide open when they aren’t home?

“Dean? What the hell are you doing in my house?” Dean turns around at the sound of Benny’s annoyed voice and sees him standing in the door.

“Uh I thought this was the open house? It was literally open,” he stammers. “Why was your door open? You know what? I’ll go, I should go. See ya. Or not, whatever.” Benny stares at him, but doesn’t move to let Dean by. Cas chooses this moment to come down the stairs, and if Benny’s eyes were wide before, they’re wider now.

“And who are you? Dean, what is going on?” Dean looks to Cas and back at Benny. Cas narrows his eyes at Benny and it’s a relief to see that glare in someone else’s direction for once.

“I’m Castiel. Dean’s neighbor,” he says.

“Cas, this is Benny,” Dean tells him quietly. A look of understanding crosses Cas’s face, and then one of confusion.

“Why are we in Benny’s house?” he asks, tilting his head to the side.

“That’s what I’m trying to find out,” mumbles Benny.

“I _told_ you. And we’re leaving,” says Dean, ushering Cas out the (still open) front door, which gets shut behind them before Dean can turn around and do it himself. Once outside, Dean turns to Cas. “So, I’m guessing that’s not the open house?”

“I’m sorry, Dean, I thought it was the right address…” Cas’s pout is absolutely _not_ cute and Dean pointedly ignores his puppy dog eyes (an expression he has become immune to, due to long exposure to Sam).

“It’s fine, it’s just running into Benny all over the place is getting creepy. He probably thinks I’m stalking him now,” he says.

“A stalker wouldn’t be waiting inside a person’s house. Well, maybe they would. But probably not in the open like that,” says Cas, somewhat reasonably. 

“Thanks for the support.”

Next door, a woman is leaving a house with a ‘For Sale’ sign out front. “Jesus fucking Christ, Cas. We’re idiots,” Dean says, watching Cassie walk to a car parked on the curb.

“I’m assuming that’s Cassie,” he says. “To be fair, the sign could be referring to either house.” Dean side eyes him and hurries down the sidewalk to catch Cassie before she drives off. He makes it before she gets in her car.

“Dean? Wow, it’s been so long!” she says. “What’re you doing here?”

“I have a – uh friend who lives next door to you. I had no idea you lived around here.” He glances at Cas, who is standing near him, but a bit behind, and watching little kids fly kites across the street. “How are you?”

“I’m doing okay, now. Been going through some stuff,” she says vaguely. “I thought you were overseas! Are you out of the army?” she asks.

“Yeah, yeah, I’m back home for good,” he says. He’d nearly forgotten about the elaborate lie that ended their relationship, not that she’d ever found out the truth, obviously.

“That’s great. We should catch up,” she says. “Are you busy tonight? We can meet for dinner.”

“I can do that,” he says. He gives her his cell number and she types hers into his phone. “Just text me a time and a place.”

“Sounds good,” she says. “I have to go, but I’ll see you tonight.” Cassie’s smile is radiant as she slides into the driver’s seat.

“Army?” asks Cas, eyes bright.

“Shut up,” says Dean. “She had a thing for the uniform. It was also a handy excuse to break up with her without her really realizing it.”

“Dick move,” says Cas.

“Yeah, I’ll admit I was a dick,” agrees Dean.

“ _Was_?” asks Cas. Dean rolls his eyes and starts walking down the street away from Cas, who catches up easily.

“I looked good in the uniform, though,” he says.

“I’ll bet.”

~*~

Cas is heading out of his apartment when Dean gets to the top of the stairs after his dinner with Cassie. He’s holding his guitar and wearing sweatpants, so it doesn’t look like Cas is going _out_.

“How was the date?” asks Cas.

“I wouldn’t exactly call it that,” says Dean.

“Why not?”

“She freaked out pretty good when I accidentally let slip that I’d uh never been in the army and I had made the whole thing up.”

“Accidentally let slip?”

“I had to tell her! She hates me now, but it feels good to have that off my conscience.”

“I’m sure it was really eating at you.” Dean doesn’t appreciate the sarcasm.

“I always kinda felt bad about it. I wasn’t ready for a long term relationship and she was getting serious… I panicked. There’s no coming back from this though,” says Dean. He unlocks his door and tosses his wallet, keys, and phone on the kitchen counter. Dean isn’t surprised to see that Cas has followed him inside.

“Well, you had to come clean. Obviously you couldn’t have a relationship with her with a lie as big as that hanging over your head,” says Cas. “Why did you want to meet up with her again?”

“I don’t know… foolish optimism?” Dean flops onto his couch, legs over the back of it. Cas sets down his guitar, but Dean can’t see what he’s doing from his position.

“Did you make this?” asks Cas softly. He sounds impressed, so Dean rolls off the couch and stands up to see what he’s talking about. He feels overdressed standing next to Cas in his nicest jeans and button up shirt, while Cas is wearing a well-worn t-shirt and sweats, feet bare. He shakes his head minutely and remembers what he’s supposed to be doing, which is not checking out Cas, which isn’t what’s he’s doing anyway, so. Cas is holding a wooden sculpture, one of many cluttering up available counter space in Dean’s apartment. This particular one is an abstract interpretation of an octopus, meant to be more than a little unnerving. The other sculptures are various animals done in the same style. Dean’s favorite is a two foot bear he’d done not long after breaking up with Benny, now he thinks of it.

“I did, yeah,” says Dean, finally. Cas squints at it, assessing the sculpture with the same level of intensity he usually reserves for Dean.

“What did you say you did, again? The job you were fired from,” asks Cas.

“Oh, uh, marketing,” he says. “Why?”

“You could make a career out of this, Dean. You’re incredibly talented,” says Cas, seriously. He’s moved on to check out Dean’s other shelves. Dean’s cheeks heat up and he avoids Cas’s eyes, not that they’re focused on him at the moment.

“Nah, I don’t think I could make any real money out of it,” he says, picking at the button on his cuff. He talked to Anna about this once, she was all for trying to get Dean to pursue art, but he hadn’t listened to her. His parents accepted his hobby, but he couldn’t imagine what his dad would think if he told him he wanted to be an artist. Sam would tell him to go for it if he knew he was thinking about it.

“Don’t do it for the money, then,” says Cas.

“Maybe if we lived in a perfect world,” says Dean. Cas levels his stare at Dean once again, but doesn’t say anything else about it. He picks up his guitar and makes to leave, but then he turns back to Dean.

“Are you coming?”

“Where exactly are we going?” he asks.

“Just follow me.”

Figuring he’s got nothing left to lose tonight, he does.

They climb the stairs all the way up and Dean follows Cas through the door to the roof. It’s completely dark outside, and clear, so some stars are visible despite the light pollution from the city. There’s a nice breeze, and while Dean feels comfortable, he worries a bit about Cas’s bare feet.

“I thought residents weren’t allowed up here,” says Dean. Cas goes to sit on a couch, and it’s even on a large rug. There are a few potted plants and a line of string lights to see by.

“They are,” says Cas. “I was the one who passed that rumor around so no one else would come up here.” Dean laughs, of course he did.

“And what do you do up here by yourself?” he asks.

“Play guitar. Look up at the stars,” says Cas. “My band practices here, usually.”

“Is that couch something I want to sit on?” asks Dean, warily.

“I don’t bring anyone else up here,” he assures.

“No? It’s kinda romantic,” says Dean. He blinks. “Uh, not that – ”

“I don’t think my ‘conquests’ are looking for romance,” says Cas, unperturbed by Dean’s observation.

“Don’t want to soil your special place with meaningless sex, huh?” He joins Cas on the couch and watches Cas pick at the strings on his guitar, not really playing. He has good hands for it. Guitar playing, that is.

“Do you have a special place?” asks Cas. He begins to pluck out a tune that sounds unfamiliar to Dean. It might be a Cas original.

“My car, maybe. I don’t drive as much, anymore. I like the feeling of the open road,” he says. “Or the headspace I get into when I’m carving with the record player on.”

“What kind of music do you like, Dean?” asks Cas.

“All sorts,” he says. “Know any Led Zeppelin?” He grins over at Cas, who nods before starting “Stairway to Heaven.” He leans back and looks up, street noise lost to the music. Dean’s heard the song a thousand times, but it sounds different on Cas’s guitar, here, under the stars.

**Notes for the Chapter:**

> this thing is like all dialogue oops
> 
> we're probably looking at seven chapters now (or longer chapters)
> 
> thanks everyone for reading and leaving kudos ♥


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